Quinoline-oxazoline compounds and their use in oxidation synthesis

Abstract

A quinoline-oxazoline compound having the formula: where one of X 1 and X 2 is N and the other is C and one of R1, R2 and R3 is Z wherein Z is an oxazoline radical having the formula such that when X 1 is N R2 is Z and R1 is absent, and when X 2 is N either R1 or R3 is Z and R2 is absent. R1 and R3 through R12 are independently H or a pendant moiety which does not interfere with coordination of either N in the quinoline compound with a coordination center. These compounds can be complexed with a suitable coordination center such as catalytically active palladium and can be highly useful in catalytically oxidizing alkenes with high regioselectivity.

1. A method of catalytically oxidizing an alkene, comprising:
 a) exposing an alkene to a quinoline catalyst complex in the presence of a mediation compound to form a ketone, said quinoline catalyst complex including a coordination center complexed with a quinoline compound having the formula 
 
       
         
           
           
               
               
           
         
         
           where one of X 1  and X 2  is an N and the other is C and one of R1, R2 and R3 is Z wherein Z is an oxazoline having the formula 
         
       
       
         
           
           
               
               
           
         
         
           such that when X 1  is N R2 is Z and R1 is absent, and when X 2  is N either R1 or R3 is Z and R2 is absent, and R1 and R3 through R12 are independently H or a pendant moiety which does not interfere with coordination of either N in the quinoline compound with the coordination center. 
         
       
     
     
       2. The method of  claim 1 , wherein the quinoline compound is a quinoline-2-oxazoline having the formula: 
       
         
           
           
               
               
           
         
       
     
     
       3. The method of  claim 2 , wherein R3 through R12 are hydrogen. 
     
     
       4. The method of  claim 2 , wherein R3 through R8, R11 and R12 are hydrogen and R9 and R10 are methyl. 
     
     
       5. The method of  claim 1 , wherein the quinoline compound is a 1-isoquinolineoxazoline having the formula: 
       
         
           
           
               
               
           
         
       
     
     
       6. The method of  claim 5 , wherein R3 through R12 are hydrogen. 
     
     
       7. The method of  claim 1 , wherein the quinoline compound is a 3-isoquinolineoxazoline having the formula: 
       
         
           
           
               
               
           
         
       
     
     
       8. The method of  claim 7 , wherein R1 and R4 through R12 are hydrogen. 
     
     
       9. The method of  claim 1 , wherein R1 and R3 through R12 are independently selected from the group consisting of hydrogen, lower alkyl, aryl, and halide. 
     
     
       10. The method of  claim 9 , wherein R1 and R3 through R12 are each hydrogen. 
     
     
       11. The method of  claim 9 , wherein at least one of R1 and R3 through R12 is methyl. 
     
     
       12. The method of  claim 11 , wherein R9 and R10 are methyl. 
     
     
       13. The method of  claim 9 , wherein at least one of R1 and R3 through R12 is a lower alkyl having up to 8 carbon atoms. 
     
     
       14. The method of  claim 9 , wherein at least one of R1 and R3 through R12 is aryl. 
     
     
       15. The method of  claim 9 , wherein at least one of R1 and R3 through R12 is a halide selected from the group consisting of fluorine, chlorine and bromine. 
     
     
       16. The method of  claim 1 , wherein the quinolone catalyst complex further comprising the coordination center coordinated with each of the N in the quinoline compound. 
     
     
       17. The method of  claim 16 , wherein the coordination center is a metal. 
     
     
       18. The method of  claim 17 , wherein the metal is palladium, platinum, rhodium or nickel. 
     
     
       19. The method of  claim 18 , wherein the palladium is palladium (II). 
     
     
       20. A quinoline compound having the formula: 
       
         
           
           
               
               
           
         
         wherein R1 and R4 through R12 are hydrogen. 
       
     
     
       21. A quinoline compound having the formula: 
       
         
           
           
               
               
           
         
         where one of X 1  and X 2  is an N and the other is C and one of R1, R2 and R3 is Z wherein Z is an oxazoline radical having the formula 
       
       
         
           
           
               
               
           
         
         such that when X 1  is N R2 is Z and R1 is absent, and when X 2  is N either R1 or R3 is Z and R2 is absent, and R1 and R3 through R12 are independently H or a pendant moiety which does not interfere with coordination of either N in the quinoline compound with a coordination center and at least one of R1 and R3 through R12 is a halide selected from the group consisting of fluorine, chlorine and bromine.